The Many Men of Lorelai Gilmore
by reviewgirl911
Summary: Lorelai Gilmore has had many men, but only three have ever really mattered.


**A/N: Hey! This is just a one-shot I randomly thought of. Since Gilmore Girls is what introduced me into the wonderful world of fanfiction, I figured that it was time for me to actually write about it. This is centered around Lorelei and her history with men up to the kiss at the end of season four.**

**Disclaimer: I don't own Gilmore Girls. Sometimes I feel like I'm living it though. *pauses* Like no joke. My mom and I are Lorelei and Rory. **

Lorelai Gilmore has had many men in her life, but only three of them ever really mattered.

Like every little girl on the planet, the first man she loved was her dad. She looked up to him like a god. Mr. Gilmore was a smart, successful man who always made sure his wife and daughter had everything they desired. Who wouldn't love that? One day, she snuck into his office and stole his Yale diploma, saying that she wanted to be just like him one day. She knew that was the proudest her father ever was of her. As she got older, Lorelai noticed that there were certain things other children got that she never received. Hugs and kisses were rare in the Gilmore mansion, and family outings even rarer. She wasn't allowed to play outside because of the restricting new dress her mother made her wear. Worse of all, her father, her hero, pretended not to listen when her mother lectured her and when she cried in her bedroom. So, by the age of eight, Lorelai had fallen out of love with her father.

The second boy she ever fell in love with was Christopher Hayden. She remembered being nine years old and him chasing her around her backyard while their mothers watched and gossiped. It was a rare moment that Emily Gilmore actually looked after her daughter. Lorelai was usually left in the care of whatever nanny was hired that week. She remembered running and screaming because he said he was going to kiss her. It would be many years later when she realized that she wanted him to.

Lorelai grew up and started to rebel against her parents. Growing up in the Gilmore mansion had always been dull, but now it seemed unbearable to the thirteen-year old girl, which was why she was intrigued by a boy only two years older than her who worked at the country club. For once, she actually pleaded for her father to take her to the country club. Richard Gilmore happily agreed, thinking his daughter was finally adapting into their world. If only he had known. The boy, Nick, was her first kiss. It was a pretty good kiss, soft and sweet, long but not too long. They had a few more meetings and kissed a few more times before he moved to Indiana.

By her freshman year of high school, Lorelai was an expert in kissing. Her favorite boy to kiss then was Peter Cutler. She met him one night at a party she wasn't supposed to be at with a friend. She had said something sarcastic, and he had laughed in appreciation. Peter was older, a senior, and there was a dangerous edge to him Lorelai appreciated. Most of the time they hung out in a group, smoking and drinking in the back of Peter's banged up truck. She liked kissing him. He didn't treat her like some porcelain doll, and she didn't expect him to. Lorelai wouldn't call him her first boyfriend because he wasn't even that. Peter was just the cute boy she let grope her while getting drunk in the back of his trunk.

By sixteen, Lorelei was much more experienced than her parents would ever like to think. She was still a virgin, of course, but there had been many boys touching her lips and other places. Fortunately, the only boy she wanted to kiss by sixteen was Christopher. His kisses were soft and gentle, and they made her wonder what would've happened if she had let him kiss her when they were nine. Christopher's kisses weren't sloppy and wet like the other boys who just wanted to coup a feel before moving on to the next girl. He touched her like she was some kind of precious gem too valuable to even scratch, and she fell in love with him for it.

Everyone thought Lorelai and Christopher were the perfect couple. Both came from prominent, wealthy Connecticut families. Their fathers did business together, and their mothers were co-chairs on practically every committee and board. It was a society match made in heaven. Their personalities matched up as well. Christopher lived in Lorelai's crazy world of pop culture, and the couple shared the same reckless streak that drove their parents mad. Lorelai and Christopher had so many adventures that she started to forget which ones her parents knew about and which they didn't. Together the couple made plans to escape the suffocating blue-blood world they had been forced into. They dreamed of park benches in Paris and hostiles in Italy, dancing in the rain in London and discovering mummies in Egypt. Lorelai made a list of places she wanted to go, and Christopher promised to take her there. The first place on the list was anywhere but Hartford. Christopher took her to the small town that would later be her town. There was some kind of festival going on, and they just sat in his car and watched the people in front of them. Lorelai never felt more in love with him than that day.

And then they started to have sex. Their first time was painful and awkward and amazing and terrifying. It happened on the balcony, their spot for so many years. Lorelei had been arguing with her parents again, and he had found her up there staring at the stars. One kiss led to another, and before she could comprehend what was happening, her bra was on the ground. Lorelei kissed Christopher slowly, and he looked at her like she was the most beautiful thing on the planet. She never forgot that moment even after everything else that happened afterwards. She had never felt so special in her entire life. The couple had sex a few more times, but those times never compared to that.

Lorelai's world came tumbling down when her dress didn't fit and the blue lines appeared on her pregnancy test. She was sixteen and pregnant. Lorelai wasn't a stupid girl. She knew this would change her life forever. She knew it would possibly destroy her relationship. She broke the news to Christopher as gently as she could. He promised to support her no matter what decision she made. Lorelei didn't even have to think about it. She was keeping the baby. It was a part of her and Christopher. She didn't have the heart to get rid of it, though she knew it would be the smart thing to do in her case. They told their parents and watched as a new world war erupted in the Gilmore's living room. The couple watched from the stairs as their parents rearranged their lives for them. Christopher saw it as an easy solution, a good plan. Lorelai saw it as one more way to control her. She wasn't ready to get married and neither was Christopher. She wanted him to sleep a park bench in Paris and see the world, not take a job at her dad's company. It felt like everything she loved about him faded the bigger her baby bump got. By the end of her pregnancy, Lorelai was determined not to marry Christopher despite the prodding from her parents and friends.

Christopher wasn't there when she had Rory. Truthfully, this didn't really surprise her. He had gotten more and more distant as the months went on, not going to a single doctor's appointment with her or talking about the future without proposing. After Lorelei gave birth to Rory, she rejected Christopher's proposal one last time. It broke his heart to see his rejected face, but it had to be done. He finally got the hint, soon graduating high school and heading off to college. It was just her and Rory.

Raising Rory in her parents' house was a nightmare. Lorelai was determined to give Rory a different upbringing than she had been given, but Emily derailed her at every turn. Lorelai said she didn't want a nanny; her mom goes and hires one. There were too many restrictions and no escapes this time. After a year of what she came to refer to as Hell, Lorelai took a baby Rory and left the Gilmore mansion for good. She hopped on a bus and got off at the first town, the same little town Christopher had taken her to for the festival.

Lorelai didn't meet Luke until Rory was eleven. She had been late for work at the inn and in desperate need for coffee. A small little diner popped out at her, and she went inside. The place had been packed, and there was only one guy in flannel and a backwards baseball cap working. She assumed that guy was Luke and went up to him, begging him for coffee. He said that he was busy and to wait her turn. An idea popped into her head. She kept pestering him, asking what his birthday was. Finally, Luke got annoyed and told her his birthday. She borrowed the horoscope section from some guy eating at the counter, ripped off the Leo horoscope, and wrote something on it. Lorelei handed it to him and waited. Luke looked up at her with something that resembled a smile and gave her a cup of coffee. That night, she brought Rory to the diner for dinner. A friendship had been built.

For many years, Luke was the only constant man in her life, the only one she could bring herself to count on. He acted as a father figure to Rory, a spot that desperately needed filling due Christopher's sparse involvement in his daughter's life. It always broke her heart to hear her pretty little girl ask why her daddy didn't love them. Lorelei couldn't give her an answer, only reassuring the young girl who looked so much like Christopher that she had plenty of love around her. Luke acted as a friend to her, and as the years went by, their friendship grew stronger. In fact, looking back later in life, Lorelei guessed that the reason she didn't date for so many years of her daughter's life was because she had Luke to fill the void a boyfriend would. Sure, she had the casual fling here and there, but there was nobody she'd introduce her friends or Rory to.

Max was the first man to really get past her walls since Christopher. Every voice in her head screamed for her to walk away. He was Rory's teacher, and she had a feeling the other Chilton moms wouldn't be too keen on the idea. Still, something about him fascinated her, and she found herself accepting his offer of a date. Though the actual date took a while to set up, Lorelei found herself enjoying a real relationship for the first time in sixteen years. She was surprised how fast it actually happened. Suddenly she was sixteen all over again. Only this time, there were no balconies or escape plans. With Max, there were secret calls while he was at school and home cooked meals followed by sex at his apartment. Lorelei wasn't sure what she enjoyed more, the sex or the food.

Sex with Max was different than it had been with Christopher. He was more experienced and knew exactly how to guide her. For the first time, she actually had screams of pleasure in bed. Then again, that could just be the fact that sex was infinitely more enjoyable as a thirty-two year old than a sixteen year old. Lorelai wasn't sure if she loved Max, but she knew she cared about him.

Rory calling him Max, however, set off so many sirens in her head. She had kept her daughter out of her relationships for a reason. Lorelei was smart enough to know that no guy she dated was guaranteed to be permanent. She told Sookie that she was afraid of Rory getting attached to Max, but she also was afraid of getting attached to Max and losing the freedom she had fought so hard for. So Lorelei pulled away and Max let her go. She cried and fell apart, feeling a hot flash of shame when her teenage daughter started to comfort her.

And then Christopher came to Stars Hallow. A part of her heart seemed to shatter at the sight of him. It was easy to forget the past when it was on the other side of the country, but seeing him right in front of her with that smirk of his was almost too much for her to handle. He didn't look different. He never did. Rory's face lit up, and there was another bang in her chest. It was times like this that she wished she had married Christopher if only so she could see that smile on her daughter's face all the time. Sure, the two of them had a pretty good life, but there were things missing that neither of them ever brought up. The presence of Christopher in her house, though unsettling, felt right somehow.

Truthfully, Lorelai doubted his seemingly fake sincere reasons for being back in Connecticut. The more likely reason was that his latest business venture had gone bust and he was back to convince his parents to give him more money. It turned out she was right. Lorelai laughed to herself while thinking about how her parents saw Christopher as the success. Sometimes, she mused, they forgot his part in Rory's creation. She never forgot, though the sex on the balcony refreshed her memory a bit. It had been a stupid thing to do, but it felt comfortable and familiar. He still looked at her like she was still the most beautiful thing he had ever seen.

Lorelai was thrown for a loop when Christopher proposed. She had just had an argument with Luke, and it didn't feel right. The teenager in her screamed for her to say yes, but it was the adult in her that prodded her to say no and tell Christopher off. That was their problem: Lorelei had grown up too much and Christopher hadn't at all. He left as quickly as she came, and Lorelei tried to forget.

There was a disastrous blind date and a few flirtations before something drove her back to Max. Maybe it was Rory's three month anniversary with Dean, something she hadn't had since Christopher, or maybe it was Rachel's return to Stars Hallow. Either way, Lorelei was sick of being alone. Being back with Max was great, but the old issues were still hanging in the air. He wanted more and more, and she wasn't as willing to give.

Max's proposal stunned her. More importantly, it confused her. Lorelei cared about Max, she knew that, but she wasn't sure if she loved him. On the other hand, she knew she wasn't going to be young forever and Max was good to her. Rory and Lorelai's friends liked him. He could deal with her parents. Everything seemed right. It wasn't until her talk with Luke that she realized what was missing. A certain spark, something that would make her miss him when he was away. Lorelai didn't love Max.

It took a while after she canceled the wedding to start dating again. Her first date afterwards was with the guy from her business class, something she got so much crap for later. Really, Lorelei just wasn't interested in another relationship so quickly. She tried to focus on opening her own inn with Sookie, a recent dream of theirs.

Lorelai was wary of Jess for many reasons. The first few had to do with the overprotective mother in her, but the others had to do with the teenager in her. Jess reminded her of another world, one she was trying to forget. He reminded her of Peter Cutler and sneaking booze at one of the nauseatingly boring debutante balls. What really scared Lorelai was Rory's reaction to Jess. He provoked something within the bookish girl, and she stayed up worrying about her daughter's future. Lorelai had always though Rory would fall for a bad boy at one point, but she had hoped it would be a quick phase, not a long-boiling infatuation. Lorelai prayed to the God she wasn't sure existed that Rory be spared the heartache she had experienced.

In the time she was dealing with Rory's love life, Christopher came back, and for once he had his life together. Lorelai was hopeful until she saw the gorgeous woman standing next to him. He gotten his life together, but he had done it with someone else. She tried not to be jealous and vindictive when Sherri wanted to hang out with Rory, but it didn't feel fair to her. She couldn't get Christopher and Rory. Lorelai was nervous when she told Christopher the reason she hadn't been able to be in a relationship for so long. His reaction wasn't what she expected. He snapped at her, and it was weeks until they talked again.

Lorlelai blamed Jess and in turn Luke for the car accident because she didn't want to admit she had failed her job as a mother. It was her job to keep Rory safe. Still, she yelled at Luke and blamed Jess because there was nobody else to turn the blame on. Of course, Luke didn't react well, and it was weeks until they would really talk again.

And though Luke had walked out of her life, Christopher was suddenly back in it. And while a part of her heart whispered that it wouldn't last, that it never did, she enjoyed the time he was there. The night of Sookie's rehearsal dinner made it feel even more real. Christopher told her that he was leaving Sherri, and Lorelai actually let herself believe that they could be a real family. She would never admit it, but the blue-eyed woman had always dreamed of having a normal little family: husband, wife, daughter, Jeep. It felt like she was closer to that dream than ever.

The night they spent together at the Inn felt magical. The sex was even better than the sex on the balcony, and Lorelai loved how he touched her like she was glass. She felt sixteen and free. Of course, something should've told her that it wouldn't last. It never did.

Lorelai felt like someone had punched her in the gut when Christopher said Sherri was pregnant. It was like karma's way of saying, 'Screw you, Lorelai Gilmore.' She said congratulations in a desperate clipped tone that only slightly betrayed the emotions she was feeling. It hurt that Christopher used her at a reason to go back to Sherri. He was willing to be with Sherri and be a father, but he had never supported her like that. Once again, Lorelai felt second best in Christopher's life.

She made up with Luke the night of the Summer Madness festival. She had gone into the diner, desperate for a cup of coffee. Luke had refused to talk to her at first. Lorelai then told him to think of him as a new customer named Mimi. 'Mimi' poured her heart out to Luke, telling him her fears and insecurities. He reacted by giving her a free cup of coffee. Their friendship was restored.

Lorelai had never been angrier in her life than when Christopher showed up at her mother's house. Avoiding his calls should've made it clear that she didn't want to talk to him. And yet he had the nerve to show up at her parents' house and yell at her? To accuse her of keeping Rory from him, something she would never do? Hell, she's had to fight Christopher to be in his daughter's life. Lorelai was proud of Rory when she snapped at Christopher. It made her feel good and victorious to have her daughter state that she was the only parent she needed. Still, something inside Lorelai made her reassure Christopher that Rory would come around. And once again he hopped on his motorcycle and drove off.

The sting of Christopher leaving her once again influenced her love life, or lack of a love life, that year. Of course, Lorelai liked to tell herself she was just too worried about Rory and all the drama of college applications and boys. She was unnerved when Rory and Dean broke up and even more unnerved when her little angel got together with Jess. Of course, she should've seen it coming but still. Lorelai just hoped he wouldn't break her heart. She already knew the ending to that particular story.

And then she met Alex at the community center, and it was simple. He was a nice guy, and she needed a nice guy for once. Lorelai liked Alex because they both knew the limits of the relationship. They got coffee, went on dates, had sex, and didn't expect anything more of the other person. And when it finally faded away, neither of them was heartbroken. It was a very low maintenance relationship.

Having to be there at the hospital with Sherri was like a knife in her stomach, but Lorelai had to do it. She had been alone in labor and would be damned if anyone else had to be. Still, she wanted to scream when Christopher ended up getting there on time. It wasn't fair. He had never been there for her, supported her. He didn't care when Rory had been born, so why she care about his new daughter? Lorelai left the hospital as soon as she could.

And then suddenly Max was back at Chilton, and something in her heart kept screaming, 'It's a second chance!' She kissed him on impulse and would've gotten back together with him right then and there, but something in her heart was still missing when they kissed.

On top of everything, the Inn burned down, and Lorelai found herself truly lost for the first time in many years. The Inn had been her refuge from the confining world of her childhood and bad omens seem to come with its demise. She stayed with Luke that night and was once again reassured by his friendship. Discovering Nicole didn't like her, however, came as a bit of a shock. Apparently the lawyer was jealous since Luke had mentioned her on their first date. What an idiot. You never talk about a female friend on a first date. Hell, you shouldn't even talk about your mother on a first date!

And then Rory went off to Yale and she was left alone. It was an adjustment getting used to living alone the first couple of months. Lorelai had never truly lived along before. She'd gone from living with her parents to living in the potter's shed with Rory to living in their house. Some nights, it spooked her, and she'd call Luke to come stay with her, which he always did. Luke always came over when she called.

When Lorelai found out what Jason Stiles did to her mother and indirectly to her, she was furious. Her plans for the Inn were more expense than she had expected, and her mother's money would've really helped her out. But no, Jason had to go and screw her over. She went to his office and started yelling at him, pulling out old childhood nicknames and antidotes as insults. To her surprise, Jason played her game, throwing out quips almost as fast as she could. And somewhere in the very back of her mind, Lorelai found herself attracted to Jason.

Of course, she made him work hard for a date for a few reasons. The first was that she was still pissed off and wanted to make him suffer, but the second was much more sensible. She simply wanted to make sure he was for real and not just playing with her. For once, she wanted a man to have to work to go out with her. Of course, Emily's disapproval is what pushed Lorelai right into Jason's arms. She felt like a teenager again but in a good way. It felt good to flip the bird to her mother.

Jason was smart and successful, if not a bit odd, and he knew how to treat a lady. It was nice to date a man with ambition, one with goals and plans, after dating so many, to put gently, losers. He made her laugh and could cook. The sex was pretty good too, and the whole relationship was powered by the secret element. Lorelai had always loved sneaking around and had thrived on it as a teenager. If her parents told her she couldn't do it, she went out that night and did it anyway.

Sometimes, though, she felt like they were doomed because they came from the same world. Jason knew certain things about her knew, knew the wild teenage girl who'd flashed boys from the canoes. Lorelai felt like she had to push so hard to make him forget all that. It didn't seem worth it.

Still, it did shock her when everything blew up in her face. She had been so happy with the Inn finally up and ready to open that it completely blindsided her. Lorelai's only priority had been her Inn. Of course, after the incident, she didn't invite her parents or Jason to the grand opening. Of course, Jason showed up anyway, but that was a whole other story. Lorelai felt sad that she didn't have anyone to share her success with until she realized she did: Luke.

Luke had been there through the whole process with her. He had watched her freak and stress over small details and had comforted her when it all seemed to get to be too much. He even loaned her $50,000 when she mentioned it crying like an idiot. It was Luke. It had always been Luke.

The kiss by the doorway was unlike any she had ever experienced. It wasn't wet and sloppy like Peter's or gentle like Christopher's or mechanical like Max's. It was passionate, hungry, and just the kind of kiss she'd always wanted. And when Kirk ran out of the Inn naked and screaming, Lorelai realized the only man she wanted to be with was Luke. It was a shocking realization, one she didn't see coming, but it was true.

Lorelai Gilmore has had many men and kissed even more, but only three men ever mattered. And out of those three men, only one ever stayed. And Lorelai was determined to keep Luke there as long as she lived.


End file.
